In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

I’m not sure all of the regulations/rules to this in PA though.

The combination of Germany's stable economy, well-regulated property market, relatively low interest rates, and the opportunity for long-term capital appreciation make it a compelling choice for U.S.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

Once you hit a certain number of loans (check with your state dept of banking and finance or dept of business regulation), they might require you to have a license.

Now, you can get some wholesalers but they usually don't know if the property will fit the requirements and regulations but you can learn that from the Realtor. 

The first thing here would be the regulations and laws governing acquiring properties, managing properties and selling properties.

I'm not familiar with Canadian regulations but you should look into how you can get access to money if you don't have any.

As more people placed more properties in STR inventory, and as more municipalities taxed and regulated the industry, the profitability of the overall industry has reverted to a much more aligned (lower) risk adjusted return.  

You also need to consider any STR regulations.